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Busulfan

Busulfan Structure
Busulfan
  • CAS No.55-98-1
  • Chemical Name:Busulfan
  • CBNumber:CB2105891
  • Molecular Formula:C6H14O6S2
  • Formula Weight:246.3
  • MOL File:55-98-1.mol
Busulfan Property
  • Melting point: :114-117 °C(lit.)
  • Boiling point: :359.3°C (rough estimate)
  • Density  :1.305 (estimate)
  • refractive index  :1.5630 (estimate)
  • Flash point: :9℃
  • storage temp.  :Hygroscopic, Refrigerator, Under Inert Atmosphere
  • solubility  :Very slightly soluble in water, freely soluble in acetone and in acetonitrile, very slightly soluble in ethanol (96 per cent).
  • form  :Crystalline Powder
  • color  :Pale Brown
  • Water Solubility  :Decomposes
  • Merck  :14,1505
  • BRN  :1791786
  • Stability: :Moisture Sensitive
  • CAS DataBase Reference :55-98-1(CAS DataBase Reference)
  • FDA UNII :G1LN9045DK
  • NCI Dictionary of Cancer Terms :busulfan; Busulfex; Myleran
  • Proposition 65 List :1,4-Butanediol dimethanesulfonate (Busulfan)
  • IARC :1 (Vol. 4, Sup 7, 100A) 2012
  • EPA Substance Registry System :Busulfan (55-98-1)
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H300-H225-H301+H311+H331-H370-H301-H310+H330-H350-H310-H330
  • Precautionary statements P202-P261-P264-P270-P271-P301+P310+P330-P302+P352+P312+P361+P364-P304+P340+P311-P403+P233-P405-P501-P210-P260-P280-P301+P310-P311-P201-P302+P352+P310-P304+P340+P310-P308+P313-P284-P302+P350-P301+P310a-P304+P340-P320-P330-P501a
Busulfan Price More Price(13)
  • Brand: Sigma-Aldrich
  • Product number: B2635
  • Product name : Busulfan
  • Purity: analytical standard, for drug analysis
  • Packaging: 10g
  • Price: $32.7
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: B1170000
  • Product name : Busulfan
  • Purity: European Pharmacopoeia (EP) Reference Standard
  • Packaging: 
  • Price: $190
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: B-058
  • Product name : Busulfan solution
  • Purity: 
  • Packaging: 058-1ml
  • Price: $202
  • Updated: 2019/12/02
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: BP403
  • Product name : Busulfan
  • Purity: British Pharmacopoeia (BP) Reference Standard
  • Packaging: 
  • Price: $226
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: B1022
  • Product name : 1,4-Butanediol Dimethanesulfonate
  • Purity: >97.0%(T)
  • Packaging: 25g
  • Price: $63
  • Updated: 2021/03/22
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Busulfan Chemical Properties,Usage,Production

  • Description Chemically, busulfan is classified as an alkyl sulfonate. One or both of the methylsulfonate ester moieties can be displaced by the nucleophilic N7 of guanine, leading to monoalkylated and cross-linked DNA. The extent of alkyl sulfonate–mediated DNA interstrand cross-linking has been shown to vary with the length of the alkyl chain between sulfonate esters, with the tetramethylene-containing busulfan showing less interstrand cross-linking capability than hexamethylene, methylene, or octamethylene analogues. Intrastrand cross-linking also occurs, preferentially at 5′-GA-3′ but also at 5′-GG-3′ sequences. Alkylation of Cys sulfhydryl groups is yet another mechanism of cytotoxicity.
  • Chemical Properties White Crystalline Solid
  • Originator Myleran,Burroughs- Wellcome,US,1954
  • Uses Alkylating agent with antileukemic activity. Antineoplastic
  • Uses Antineoplastic alkylating agent, the palliative treatment of chronic myeloid leukemia, and insect sterilant.
  • Uses Busulfan USP (Myleran) is used to treat Chronic granulocytic leukemia; other myeloproliferative disorders.
  • Indications Busulfan (Myleran) is a bifunctional methanesulfonic ester that forms intrastrand cross-linkages with DNA. The drug is well absorbed after oral administration and has a plasma half-life of less than 5 minutes. Metabolites and degradation products are excreted primarily in the urine.
    Busulfan is used in the palliative treatment of chronic granulocytic leukemia. Daily oral therapy results in decreased peripheral white blood cells and improved symptoms in almost all patients during the chronic phase of the disease. Excessive uric acid production from rapid tumor cell lysis should be prevented by coadministration of allopurinol.
    At usual therapeutic dosages, busulfan is selectively toxic to granulocyte precursors rather than lymphocytes. Thrombocytopenia and anemia and less commonly, nausea, alopecia, mucositis, and sterility also may occur. Unusual side effects of busulfan include gynecomastia, a general increase in skin pigmentation, and interstitial pulmonary fibrosis.
  • Definition ChEBI: A methanesulfonate ester that is butane-1,4-diol in which the hydrogens of the hydroxy groups are replaced by methanesulfonyl groups. An alkylating antineoplastic agent, it is used for the treatment of chronic myeloid leukemia (although it has been largely replaced by newer drugs). It is also used as an insect sterilant.
  • Manufacturing Process 3.6 grams of redistilled 1,4-butanediol were dissolved in 10 ml of pyridine and the solution was cooled in ice and water. 9.6 grams of redistilled methanesulfonyl- chloride were added dropwise at such a rate that the temperature did not rise above 20°C. The solution was then allowed to stand at room temperature to; 30 minutes, during which time the temperature rose to 60°C. A thick precipitate of pyridine hydrochloride was formed.
    The mass was cooled in ice water and was treated with 30 ml of ice cold water. On agitation, a white crystalline precipitate was formed. This was filtered off and washed well with ice cold water and allowed to drain on the pump. It weighed 7.8 grams and had a melting point of 100°C. 3.5 grams of the material were recrystallized from acetone and ether to give small white needles, having a melting point of 106°-107°C, unchanged by further recrystallization.
  • brand name Myleran (GlaxoSmithKline).
  • Therapeutic Function Antineoplastic
  • General Description White crystals or powder.
  • General Description As an alternative to utilizing aziridines as electrophilic species,it was found that simply utilizing a carbon chain terminated atboth ends by leaving groups gave compounds capable of actingas cross-linking agents.Busulfan utilizestwo sulfonate functionalities as leaving groups separated by afour-carbon chain that reacts with DNA to primarily form intrastrandcross-link at 5'-GA-3' sequences.The sulfonatesare also subject to displacement by the sulfhydryl functionsfound in cysteine and glutathione, and metabolic products areformed as a result of nucleophilic attack by these groups togenerate sulfonium species along with methane sulfonicacid.This is followed by conversion to tetrahydrothiophene,and further oxidation products are subsequently produced togive the sulfoxide and sulfone. The cyclic sulfone known assulfolane may be further oxidized to give 3-hydroxysulfolane.
  • General Description Busulfan is available as 2-mg tablets for oral administrationand 10-mL vials for IV administration in the treatment ofchronic myelogenous leukemia (CML) and in high-dosetherapy for refractory leukemia with bone marrow transplant.The agent is well absorbed when given orally, well distributedinto tissues, and crosses the blood-brain barrier.Metabolism occurs in the liver to give mainly methane sulfonic acid by the action of glutathione-S-transferase. Other identified metabolites in humanshave included tetrahydrothiophene-1-oxide, sulfalene,primarily in the urine, and the terminal elimination half-lifeis 2.5 hours. Adverse effects include dose-limiting myelosuppression;nausea and vomiting that occur commonly butare generally mild; and pulmonary symptoms including interstitialpulmonary fibrosis, which is referred to as “busulfanlung,” occurs belatedly (1–10 years posttreatment) andalthough rare, it is severe. Other adverse effects includemucositis, skin rash, impotence, amenorrhea, infertility, hepatoxicity,insomnia, anxiety, and an increased risk of secondarymalignancies. At normal doses, the agent is welltolerated except for the myelosuppression that occurs. Thishas allowed for high-dose therapy with the agent when accompaniedby bone marrow transplant to counter the myelosuppressiveeffects.
  • Air & Water Reactions Busulfan is an alkylating agent which hydrolyzes in water. .
  • Reactivity Profile Busulfan is an alkylating agent which hydrolyzes in water. . Strong reducers may yield hydrogen sulfide.
  • Hazard Extremely toxic, carcinogen, clastogenic, teratogenic, immunosuppressive, delayed bone marrow aplasia, cataracts, pigmentation, pulmonary thrombosis, cardiotoxic effects, thrombocytopenia.
  • Fire Hazard Flash point data for Busulfan are not available. Busulfan is probably combustible.
  • Clinical Use Busulfan is used in the treatment of chronic myelogenous leukemia and can be administered either orally or by IV infusion.
  • Side effects Serious bone marrow hypoplasia and myelosuppression are possible with this agent, and recovery from busulfaninduced pancytopenia can take up to 2 years.
  • Safety Profile Confirmed carcinogen producing leukemia, kidney, and uterine tumors. Experimental neoplastigenic and tumorigenic data. Poison by ingestion, subcutaneous, intraperitoneal, intravenous, and possibly other routes. Ingestion by pregnant women can cause cancer of the reproductive system of the fetus includtng the uterus. Human teratogenic effects by ingestion and possibly other routes include developmental abnormaltties of the eye, ear, craniofacial area including the nose and tongue, gastrointestinal system, endocrine system, urogenital system, and other unspecified areas. Other human reproductive effects by ingestion and possibly other routes include: impotence, changes in the uterus, cervix, and vagina, and menstrual-cycle dtsorders. Experimental reproductive effects. Human systemic effects by ingestion: general arteriolar or venous ddation of the eye, changes in structure or function of salivary glands. When heated to decomposition it emits toxic fumes of SOx. See also SULFONATES.
  • Chemical Synthesis Busulfan, 1,4-butandioldimethansulfonate (30.2.3.1), is made by reacting butandiol with methanesulfonyl chloride.

  • Veterinary Drugs and Treatments Busulfan may be useful in the adjunctive therapy of chronic granulocytic leukemias or polycythemia vera in small animals. Not commonly used in veterinary medicine.
  • Carcinogenicity 1,4-Butanediol dimethanesulfonate is known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans.
Busulfan Preparation Products And Raw materials
Raw materials
Preparation Products
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